Synthesis and Biological Evaluation of Benzodioxole Derivatives as Potential Anticancer and Antioxidant agents

• Published in: Heterocyclic Communications Vol. 26; no. 1; pp. 157 - 167
• Main Authors: Hawash, Mohammed, Eid, Ahmad M, Jaradat, Nidal, Abualhasan, Murad, Amer, Johnny, Naser Zaid, Abdel, Draghmeh, Saja, Daraghmeh, Donia, Daraghmeh, Haifa, Shtayeh, Tahrir, Sawaftah, Hadeel, Mousa, Ahmed
• Format: Journal Article
• Language: English
• Published: Berlin Walter de Gruyter GmbH 01.01.2020; De Gruyter
• Subjects: anticancer; Anticancer properties; antioxidant; Antioxidants; Benzodiazepines; benzodioxole; Biotechnology; Cancer; Cell cycle; Derivatives; Doxorubicin; Secretions; trolox
• ISSN: 0793-0283; 2191-0197
• DOI: 10.1515/hc-2020-0105

a series of benzodioxole compounds were synthesized and evaluated for their cytotoxic activity against cervical (Hela), colorectal (Caco-2), and liver (Hep3B) cancer cell lines. Compounds 5a, 5b, 6a, 6b, 7a and 7b showed very weak or negligible anticancer activity with IC 50 3.94-9.12 mM. On the contrary, carboxamide containing compounds 2a and 2b showed anticancer activity. Both 2a and 2b reduced Hep3B secretions of α-fetoprotein (α-FP) to 1625.8 ng/ml and 2340 ng/ml, respectively, compared to 2519.17 ng/ml in untreated cells. The results also showed that compound 2a has potent anticancer activity against Hep3B cancer cell line. Furthermore, in cell cycle analysis, compound 2a induced arrest in the G2-M phase in value of 8.07% that was very close to the activity of doxorubicin (7.4%). These results indicate that compound 2a has a potent and promising antitumor activity. However, benzodiazepine derivatives ( 7a and 7b) showed moderate antioxidant activity with IC 50 values of 39.85 and 79.95 μM, respectively compared with the potent antioxidant agent Trolox (IC 50 = 7.72 μM).